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WO2009108158A1 - Caoutchouc de silicone présentant une activité antimicrobienne efficace - Google Patents

Caoutchouc de silicone présentant une activité antimicrobienne efficace Download PDF

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Publication number
WO2009108158A1
WO2009108158A1 PCT/US2008/004175 US2008004175W WO2009108158A1 WO 2009108158 A1 WO2009108158 A1 WO 2009108158A1 US 2008004175 W US2008004175 W US 2008004175W WO 2009108158 A1 WO2009108158 A1 WO 2009108158A1
Authority
WO
WIPO (PCT)
Prior art keywords
silicone rubber
acid
silver
carboxylic acid
weight percent
Prior art date
Application number
PCT/US2008/004175
Other languages
English (en)
Inventor
Aijun Zhu
Yi-Feng Wang
Original Assignee
Momentive Performance Materials Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Momentive Performance Materials Inc. filed Critical Momentive Performance Materials Inc.
Priority to US12/919,609 priority Critical patent/US20110117152A1/en
Priority to CN2008801288502A priority patent/CN102014637A/zh
Priority to EP08742413A priority patent/EP2254421A1/fr
Priority to JP2010548651A priority patent/JP5323099B2/ja
Publication of WO2009108158A1 publication Critical patent/WO2009108158A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups

Definitions

  • This invention relates to a silicone rubber exhibiting effective antimicrobial activity in a microbe-populated aqueous environment to which a surface of the rubber is exposed.
  • Silver-containing antimicrobial agents have been incorporated in a variety of synthetic resins in order to provide products which exhibit antimicrobial characteristics. Although silver- based antimicrobial agents may provide suitable antimicrobial properties for some kinds of resins, it has been discovered that silicone rubbers containing silver-type antimicrobial agents often fail to exhibit significant antimicrobial activity. This lack of antimicrobial effectiveness may be due to there being relatively low amounts of silver available at the surface of the rubbers. Whatever the actual cause may be for the observed lack of efficacious antimicrobial activity in silicone rubbers containing known types of silver-based antimicrobial agents, it remains that a need exists for imparting effective levels of antimicrobial activity to silicone rubbers which are intended to utilize silver-containing antimicrobial agents that by themselves are inefficacious.
  • a silicone rubber exhibiting antimicrobial efficacy which comprises:
  • silver- containing antimicrobial substance (b) which lacks appreciable antimicrobial activity when present by itself in silicone rubber (a) exhibits a significant level of antimicrobial activity when carboxylic acid (c) is additionally present in the rubber due to the ability of the carboxylic acid to increase the availability of antimicrobial silver at the surface of the rubber, perhaps by facilitating or improving the migration of silver from within the rubber to its surface.
  • silver-containing antimicrobial agents that are known to be effective in a variety of synthetic resins but not in silicone rubber can be rendered efficacious when accompanied by a carboxylic acid.
  • silver-containing antimicrobial agent shall be understood herein to mean silver in any of its forms that exhibit antimicrobial activity in a microbe-populated aqueous environment and includes metallic silver, e.g., colloidal silver and nanosilver, silver compounds providing silver ions in aqueous media, complexes of silver, and the like.
  • carboxylic acid shall be understood herein to include mono-, di-, tri-, etc., aliphatic, cycloaliphatic and aromatic carboxylic acids and the anhydrides thereof where such exist as well as mixtures of two or more of any of the foregoing.
  • This invention encompasses a silicone rubber containing at least one silver-based antimicrobial agent that by itself exhibits little if any antimicrobial activity and at least one carboxylic acid in an amount sufficient to potentiate the antimicrobial activity of the silver-based antimicrobial agent.
  • This invention also encompasses a method of forming a silicone elastomer comprising the steps of providing a curable silicone rubber- forming composition, introducing therein at least one silver-containing antimicrobial agent in an amount of from 0.1 to 10, preferably from 0.2 to 5 and more preferably from 0.5 to 2, percent by weight, and at least one carboxylic acid in an amount of from 0.1 to 5, preferably from 0.2 to 3 and more preferably from 0.5 to 2, percent by weight, and subjecting the silicone rubber- forming composition to curing conditions to provide the silicone rubber.
  • Silicone rubber (a) can be obtained by curing any one of numerous known curable silicone rubber- forming compositions, e.g., liquid silicone rubber (LSR) compositions, room temperature vulcanizable silicone rubber (RTV) compositions and heat curable silicone elastomer (HCE) compositions.
  • LSR liquid silicone rubber
  • RTV room temperature vulcanizable silicone rubber
  • HCE heat curable silicone elastomer
  • a typical LSR composition is a multi-component combination of a vinyl-containing polydiorgansiloxane fluid, a hydrogen-containing polydiorganosiloxane fluid, an effective amount of a platinum catalyst and a reinforcing filler such as a fumed silica and one or more additional additives.
  • two-component LSR mixtures are mixed and charged into a preheated mold where they are rapidly cured to produce a silicone rubber article.
  • a first component, or package includes a vinyl-containing polydiorgansiloxane fluid, a silica filler and an effective amount of a platinum catalyst and a second component, or package, includes a hydrogen-containing polydiorganosiloxane fluid in combination with other ingredients including a vinyl-containing polyorganosiloxane fluid and a silica filler.
  • the LSR composition is produced by kneading a polydiorganosiloxane, inorganic filler and additives by means of a kneading machine such as a Banbury mixer, a turbulizer, a change can mixer or a low intensity double arm dough mixer.
  • polydiorganosiloxane, inorganic filler, treating agents and additives are batch mixed until the desired properties are obtained.
  • the batch mixing process can take 12 to 30 hours per batch.
  • the LSR composition is stripped of volatiles and cooled.
  • RTV silicone compositions may be formulated as one-component or two-component systems.
  • a common form of one-component RTV silicone, curable by exposure to moisture, includes an organosiloxane polymer possessing terminal hydroxyl groups, a polyfunctional organosilicone cross-linking agent and a crosslinking catalyst, e.g., as disclosed in U.S. Patent Nos. 4,100,129, 4,593,085, 5,420,196, 5,932,650 and 6,737,494, the entire contents of which are incorporated by reference herein.
  • Two-component RTV silicone systems typically comprise an "A" package containing a dihydroxy or silanol-terminated polydiorganosiloxane, a semi- reinforcing filler such as calcium carbonate or ground quartz, a reinforcing filler such as fumed silica and water and a "B" package containing a T or Q functional crosslinker and a condensation cure catalyst, e.g., as disclosed in U.S. Patent No. 4,490,500, the entire of contents of which are incorporated by reference herein.
  • HCE compositions generally consist of a diorganopolysiloxane gum, fluid, filler and, optionally, a curing agent such as an organic peroxide.
  • a curing agent such as an organic peroxide.
  • the curable silicone elastomer-forming composition can also contain one or more known and conventional additives, e.g., UV stabilizers, antioxidants, colorants, fillers, reinforcing agents, etc., incorporated in the usual amounts.
  • additives e.g., UV stabilizers, antioxidants, colorants, fillers, reinforcing agents, etc.
  • the silicone rubber of the invention is useful as, or in, many kinds of articles for which efficacious antimicrobial activity is a necessary or desirable property, e.g., medical and diagnostic instruments, catheters, wound care and medical dressing products, scar care management products, drug delivery systems, and the like.
  • Useful silver-containing antimicrobial agents include silver-containing inorganic compounds such as silver zirconium phosphates available from Milliken & Company under the tradename ALPHASAN.RTM. RC-2000, RC-5000 and RC-7000; silver-containing organic compounds such as silver carboxylates, e.g., silver benzoate, silver citrate and silver tartrate; silver-substituted zeolites available from Shingawa under the tradename ZEOMICRTM; silver- containing glasses available from Ishizuka Glass under the tradename IONPURE.RTM; AMP.RTM T558 and MICROFREE. RTM, both available from DuPont, and JMACRTM, available from Johnson Mathey; and, metallic silver materials such as colloidal silver, nanosilver and silver alloys.
  • silver-containing inorganic compounds such as silver zirconium phosphates available from Milliken & Company under the tradename ALPHASAN.RTM. RC-2000, RC-5000 and RC
  • Average particle size of the silver-containing antimicrobial agent can vary widely, e.g., from 5 to 30 nm in the case of nanosilver and from 5 microns to 100 microns for all other forms.
  • Carboxylic acid component (c) as previously defined can be selected from any of numerous known aliphatic, cycloaliphatic and aromatic carboxylic acids possessing one or more carboxylic acid groups, the anhydrides thereof where such exist, and mixtures thereof, provided the presence of a particular carboxylic acid, carboxylic acid anhydride or mixture of particular carboxylic acid(s) and/or carboxylic acid anhydride(s) in a given curable silicone rubber- forming composition does not adversely affect its cure or the properties of the cured rubber.
  • the carbon content of the useful carboxylic acids and carboxylic acid anhydrides will not exceed 14 carbon atoms when the carboxylic acids and anhydrides thereof are of the saturated aliphatic, cycloaliphatic or aromatic variety and in the case of unsaturated aliphatic and cycloaliphatic carboxylic acids and carboxylic acid anhydrides where the presence of one or more olefinic bonds tends to lower the melting point and increase solubility, a carbon content that does not exceed 20 carbon atoms.
  • carboxylic acids and carboxylic acid anhydrides that can be utilized herein include propanoic acid, 2-methyl propanoic acid, butanoic acid, pentanoic acid (valeric acid), hexanoic acid (caproic acid), 2-ethylhexanoic acid, heptanoic acid (enanthic acid), octanoic acid (caprylic acid), oleic acid, linoleic acid, linolenic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid, cyclohexenecarboxylic acid, benzoic acid, benzeneacetic acid, propanediol acid (malonic acid), butanedioic acid (succinic acid), hexanedioic acid (adipic acid), 2-butenedioc acid (maleic acid), acetic anhydride, maleic anhydride, and the like.
  • Comparative Examples 1-16 are illustrative of silicone rubbers containing various silver-type antimicrobial agents by themselves or the aliphatic carboxylic acid oleic acid by itself and as such are outside the scope of the invention.
  • Examples 1-25 are illustrative of the antimicrobially efficacious silicone rubbers of this invention which contains both a silver- type antimicrobial agent and an aliphatic carboxylic acid.
  • Antimicrobial efficacy was determined by the AATCC 100/Film Contact Method as modified in accordance with the description of this method which follows.
  • the test method provides a quantitative procedure for the evaluation of the degree of antibacterial activity, in this case, test samples of cured silicone rubber samples, or specimens, containing a variety of silver- containing antimicrobial agents, carboxylic acids and mixtures of both.
  • Silicone rubber film of 2 mm thickness is inoculated with a known concentration of two test organisms, Staphylococcus aureus and Escherichia coli, and thereafter cut into 35 mm x 35 mm specimens.
  • a test specimen is placed in a sterile 60 mm petri dish and "floated" in a 100 mm x 20 mm petri dish containing sterile water (for humidity purposes).
  • the test specimen is then inoculated with 0.4 mL of the test organism and incubated for 24 hours after which the specimen is neutralized with Letheen broth and serial dilutions are performed. Percentage reduction and/or log reduction is reported along with the zero time count and 24 time count.
  • test samples two 35 mm x 35 mm test samples are inoculated with 0.4 mL of each test organism(one for the zero time and one for the 24 hour time).
  • test sample is neutralized with Letheen Broth and serial dilutions are performed. These plates are also incubated 48 hours at 36-38 0 C.
  • Test specimens of a conventional first LSR (Silicone Rubber A) containing nanosilver particles were prepared with the antimicrobial effectiveness of each specimen being evaluated employing the aforedescribed microbiological assay procedure.
  • the results of the assays were as follows: Table 1 : Microbiological Test Results for Silicone Rubber A Containing Nanosilver
  • Comparative Examples 7 and 8 were substantially repeated but with Silicone Rubber B and with different loadings of the silver ion-containing ceramic matrix.
  • the test results are set forth in Table 4 as follows:
  • This example illustrates a silicone rubber, specifically, LSR 2050, exhibiting high surface-available antimicrobial silver in accordance with the invention.
  • Comparative Examples 13 and 14 show that the aliphatic carboxylic acid oleic acid is not effective as an antimicrobial agent when present by itself in Silicone Rubber A but as shown in Examples 2 and 3, in combination with silver sodium hydrogen zirconium phosphate RC 2000 as the antimicrobial silver-containing agent, provides a high level of antimicrobial effectiveness.
  • the tests results were as follows:
  • Comparative Examples 13 and 14 and Examples 2 and 3 were substantially repeated but with the amounts of silver ion-containing ceramic matrix indicated in Table 7. As reported in the table, the test results were as follows: Table 7: Microbiological Test Results for Silicone Rubber A Containing Oleic Acid Alone and In Combination With and Without Silver Ion-containing Ceramic Matrix
  • Table 8 sets forth the results of microbiological testing of samples of Silicone Rubber B containing combinations of the silver ion-containing ceramic matrix of the previous examples ("Ag") with each of several different aliphatic carboxylic acids.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Toxicology (AREA)
  • Dispersion Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Materials For Medical Uses (AREA)

Abstract

La présente invention concerne un caoutchouc de silicone présentant une efficacité antimicrobienne qui contient : a) au moins un caoutchouc de silicone dérivé d’une composition formant du caoutchouc de silicone durcissable; b) au moins un agent antimicrobien à base d’argent incorporé dans le caoutchouc de silicone (a) en une quantité X en pourcentage pondéral; et, c) au moins un acide carboxylique incorporé dans le caoutchouc de silicone (a) en une quantité Y en pourcentage pondéral. L’agent antimicrobien à base d’argent (b), lorsqu’il est incorporé seul dans le caoutchouc de silicone (a) en une quantité X + Y en pourcentage pondéral, et l’acide carboxylique (c), lorsqu’il est incorporé seul dans le caoutchouc de silicone (a) en une quantité X + Y en pourcentage pondéral, ne confèrent aucune activité antimicrobienne significative au caoutchouc de silicone (a) mais la combinaison de l’agent antimicrobien à base d’argent (b) jusqu’à une quantité X en pourcentage pondéral et de l’acide carboxylique (c) jusqu’à une quantité Y en pourcentage pondéral confère une activité antimicrobienne significative au caoutchouc de silicone (a), une telle activité étant observée à l’interface d’une surface exposée du caoutchouc de silicone (a) et d’un matériau aqueux peuplé de microbes en contact avec ledit caoutchouc de silicone.
PCT/US2008/004175 2008-02-26 2008-03-31 Caoutchouc de silicone présentant une activité antimicrobienne efficace WO2009108158A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US12/919,609 US20110117152A1 (en) 2008-02-26 2008-03-31 Silicone rubber exhibiting effective antimicrobial activity
CN2008801288502A CN102014637A (zh) 2008-02-26 2008-03-31 呈现出有效的抗微生物活性的硅橡胶
EP08742413A EP2254421A1 (fr) 2008-02-26 2008-03-31 Caoutchouc de silicone presentant une activite antimicrobienne efficace
JP2010548651A JP5323099B2 (ja) 2008-02-26 2008-03-31 有効な抗菌活性を示すシリコーンゴム

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12/072,486 2008-02-26
US12/072,486 US20090215924A1 (en) 2008-02-26 2008-02-26 Silicone rubber exhibiting effective antimicrobial activity

Publications (1)

Publication Number Publication Date
WO2009108158A1 true WO2009108158A1 (fr) 2009-09-03

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PCT/US2008/004175 WO2009108158A1 (fr) 2008-02-26 2008-03-31 Caoutchouc de silicone présentant une activité antimicrobienne efficace

Country Status (6)

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US (2) US20090215924A1 (fr)
EP (1) EP2254421A1 (fr)
JP (1) JP5323099B2 (fr)
KR (1) KR20100121628A (fr)
CN (1) CN102014637A (fr)
WO (1) WO2009108158A1 (fr)

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JP2012077248A (ja) * 2010-10-05 2012-04-19 Toyo Seikan Kaisha Ltd 銀含有樹脂組成物及びその製造方法
EP2578625A4 (fr) * 2010-06-01 2014-08-06 Toyo Seikan Kaisha Ltd Composition de résine contenant des particules d'argent ultrafines
US10138038B2 (en) 2014-06-05 2018-11-27 Thomas & Betts International, Llc Antimicrobial detectable cable tie
US20190223687A1 (en) * 2018-01-25 2019-07-25 Chris Williams Floor mat and method of use
US10518950B2 (en) 2014-11-06 2019-12-31 Thomas & Betts International Llc Antimicrobial cable tie

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US20120164201A1 (en) * 2010-12-23 2012-06-28 Franco Dokmanovich Harris Method of using colloidal silver and gold anti-microbial items to create clean zones therewith
CN102863662B (zh) * 2012-09-20 2014-06-25 叶金山 一种养生保健座垫及其制造方法
US9950106B2 (en) * 2012-12-05 2018-04-24 Cook Medical Technologies Llc Antimicrobial barrier device
US9713551B2 (en) * 2014-05-16 2017-07-25 Rocktape, Inc. Kinesiology tape bandage
CN104725864A (zh) * 2015-04-08 2015-06-24 杭州歌方新材料科技有限公司 一种抗菌硅橡胶及其制备方法
EP3351105A1 (fr) 2017-01-20 2018-07-25 Kauno Technologijos Universitetas Materiaux de silicone ayant une efficacite antimicrobienne
KR102103876B1 (ko) 2018-06-04 2020-04-23 광운대학교 산학협력단 금속-유기프레임워크 포함 항균 실리콘 수지 조성물
CN111228572B (zh) * 2020-01-09 2022-04-19 天新福（北京）医疗器材股份有限公司 一种人工皮肤及其制备方法与应用
US12290625B2 (en) 2023-02-08 2025-05-06 Art Brown Collapsible mobile urine container

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EP2254421A1 (fr) 2010-12-01
JP2011513532A (ja) 2011-04-28
US20090215924A1 (en) 2009-08-27
CN102014637A (zh) 2011-04-13
KR20100121628A (ko) 2010-11-18
US20110117152A1 (en) 2011-05-19

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